This past weekend Mark went golfing with some friends, so I was left to my own vices on a beautiful, 70+ degree Saturday in October and all I wanted was to do something fall-y. I promised him we would go apple picking together, so that was out, all my friends were busy, so brewery or winery hopping was out thanks to the new regulation in Massachusetts that requires you to order food if you’re going to be drinking, and pumpkin picking alone seemed a littleeeee pathetic, even for me.
So what’s a girl to do when she runs out of ideas?
I went to another blog for inspiration! A couple months ago my friend, Retha, from the blog Roaming Nanny, asked me to contribute to a collab post she did about bucket list items in New England. As I sat at home trying to figure out how to take advantage of the beautiful day, I remembered her telling me that she had had a ton of contributions for bucket list items from Massachusetts, so off to the post I went! (You can find Retha’s blog post about Bucket List New England Items here. I wrote about the RI Brewery Passport and a lavender farm in Connecticut that basically transports you to Provence, France.)
I realized I had, thankfully, done just about everything on the list. The only two things in Massachusetts I hadn’t done yet were being a cranberry bogger for the day and hiking to the highest point in Massachusetts. I tried looking for cranberry bogger opportunities, but they’re all booked up for the season, so off to Mount Greylock it was!
Mount Greylock reaches 3,491 feet and is officially located in the town of Adams, which is in the Berkshire area of Massachusetts and is best known for its stunning fall foliage. It is about two hours from Worcester, but if you’re really after those vibrant orange, yellow, and red hues then it is definitely worth the drive!
As I do with all my hikes within the US, I turned to the AllTrails app. Since this was the highest peak in Massachusetts and I didn’t hike at all this summer outside of Joshua Tree National Park, (link here) I was looking for something relatively easy. According to AllTrails, the Cheshire Harbor Trail is a 6.2 mile out and back trail rated as moderate and is the “easiest and most direct” trail to the top of the mountain. A recent review even described the trail as being on the “easier side of moderate”, so how bad could it really be??? Six miles seemed a little long, but surely I could get it done in time to still be home for dinner.
Spoiler Alert: It was pretty rough and definitely longer than 6.2 miles. But, more on that later.
When I look for trails, I tend to look for scenic trails. Unfortunately, the Cheshire Harbor Trail isn’t known for its views…but it was October in New England so I figured the fall foliage would make up for the lack of traditional views.
After running a few errands on Saturday, I packed my bags and headed off on the two hour drive to the Cheshire Harbor trailhead with an estimated time of arrival of about noon-ish.
Whenever I plan to start hiking after 10AM I get a little paranoid that I won’t be able to find parking, especially if the drive to the trailhead will take more than a half hour. While I knew there was a strong likelihood that I wouldn’t be able to find parking, the drive alone made it worth it. The roads were lined with stunning trees in every shade of yellow, orange, and red that you could possibly imagine! It took everything I had to not just pull over and stare off into the distance.
The closer I got to the trailhead, the more I realized my fears were justified. About a quarter mile out from the trailhead I was greeted with cars parked on either side of the road, almost making it impossible to continue down the road. Thankfully when I reached the official trailhead parking lot someone was leaving and I was able to snag their spot.
Thoughts on the Cheshire Harbor Trail & Visiting Mount Greylock During a Pandemic
I was fully prepared for a 6.2 mile hike…but I wasn’t prepared for the 9.4 mile hike I ended up with.
Also, whoever described the hike as being on the easier side of moderate lied. There is maybe one or two short areas of the trail that are relatively flat, but the majority of the trail has you going up a gradual, but steep, incline the entire time. Additionally, the trail is rough. It is clearly marked, which makes navigating it easy, but there are large, loose rocks throughout that practically guarantee a twisted ankle at some point.
This trail is definitely heavily trafficked, especially on a beautiful fall day. I would say that about 75% of the people I came across had masks that they put on whenever they came across someone else. That part was great! However, I also saw quite a few people that either had no masks at all or had them hanging under their chin…but didn’t bother pulling it up when they approached me despite the fact that I made eye contact with them as I put my own on.
As I got closer to the summit, the amount of people I saw walking towards me increased. I ended up wearing my mask for a significant amount of the time I was hiking and I think that contributed to how hard it was for me to make it all the way up.
Part of the reason I am bringing up masks is because I also think this is one of the biggest reasons why my hike ended up being so much longer than expected. I normally try my best to walk straight…which, ya know, I think is a pretty normal thing to try to do. But, being in a pandemic and trying to maintain social distancing, especially trying to stay distant from people with no masks at all, I ended up weaving nonstop. Weaving during a road race always adds to the distance I actually ended up running, so I know the same thing happens with hiking.
So take this as some general advice for hiking during a pandemic: Depending on the amount of people on the trail, plan on it technically being longer than the posted distance due to the need to weave around people.
What if I’m not up for a 6+ mile hike?
Have no fear! You can drive up to the summit. However, if you’re planning on going on a weekend or during the first couple weeks of October you should be prepared for a pretty long wait. The Cheshire Harbor Trail crosses the road for the first time about a mile before the summit. When I reached that point around 2pm I overheard the woman working tell cars that it would be 45-60 minutes before they would be able to get to the top.
If you’re okay with a short hike, you can always park at that point and hike the one mile up to save a little bit of time.
The Summit
The summit of Mount Greylock gives you absolutely stunning views of the surrounding towns! You can see fall foliage for miles and it is truly awe-inspiring.
There is also a World War I memorial at the top that is beautiful!
If you’re hungry or thirsty from your hike, you can head over to Bascom Lodge for really well-priced sandwiches and baked goods. (You can even spend the night there if they have any openings!) I opted for a well-deserved peanut butter and jelly sandwich and while it was definitely delicious, the best part of the lodge is the views you get when looking out the dining room windows.
However, despite the beautiful views and delicious sandwich, I think I can officially say I am a Summit Snob.
Summits tend to be ruined for me when people are able to just drive up to them. I sweat my way up that mountain, convinced my lungs were going to give out, to reach one of the most rewarding finish lines our planet has to offer only to have it ruined by maskless people that drove up and were sprinting back and forth with total disregard for the tired hikers (or really even just the generally calm people) trying to take in the views.
I found a spot overlooking the surrounding towns to sit down and eat my lunch, making sure I had about 10 feet between myself and any other parties so we would all feel safe as I took my mask off to eat, and people with no masks felt the need to walk within INCHES of me!
I realize this sounds a little whiny, and a year ago I probably couldn’t have cared less if people came near me, but we live in a different world now and I try my best to stay at least 6 feet away from people to not only protect myself, but others as well.
Conclusion + Final Thoughts
The Cheshire Harbor Trail is not for the faint of heart, especially if it is a crowded day and you need to have your mask on, but you can definitely get it done! Just make sure you give yourself plenty of time to get up and down before sunset and allow plenty of time to enjoy the views at the top because they’re definitely worth it!
If you’re looking for scenic views throughout your hike but don’t necessarily want it to be any harder, consider switching to the Gould Trail on your way down. I actually did this by accident, but thankfully didn’t panic because I had read reviews of people that did this intentionally so I knew I would be fine.
The Gould Trail is a little more open and gives you great views of a creek that runs along the trail. When you reach the Gould Trail parking lot, you’ll be about a half mile down the road from the Cheshire Harbor parking lot. Fair warning, that half mile is straight uphill so if you plan on doing this hike I would opt to park a ways down the road away from the Cheshire Harbor lot.
Overall, this hike was beautiful and I will definitely do it again…just probably not during peak fall foliage season during a pandemic…